Secretary of State Rex Tillerson is a man with few allies. Facing bipartisan pushback from Congress and criticism from career diplomats over his prospective top-to-bottom reorganization of the State Department and swirling reports that he might step down after distancing himself from Donald Trump, Tillerson has never had less power in Washington. Even Russian President Vladimir Putin—who once awarded the former ExxonMobil C.E.O. with one of his country’s highest honors—is criticizing the embattled secretary of state.

Disappointed in the direction U.S. foreign policy toward Russia has taken under Tillerson, Putin said Thursday that it seems the erstwhile oil executive “has fallen in with bad company” since he awarded him the Russian Order of Friendship in 2013. At the time, the two had enjoyed a cordial relationship: Exxon and Rosneft, the Russian state oil company, announced a massive $500 billion deal in 2012 to develop Russia’s oil reserves in the Arctic and the Black Sea—the product of nearly a year of negotiations between Tillerson, his team, and Russian officials. The deal stalled in 2014, when the Obama administration leveled sanctions against Russia over its actions in Ukraine; relations between the U.S. and Russia deteriorated further when the Kremlin interfered in the 2016 presidential election, tipping the scales for Trump but ultimately poisoning any chance for détente. “But I hope that the wind of cooperation and friendship will blow him onto the right track in the end,” Putin added, while speaking at a business forum in Vladivostok.

Moscow initially applauded the news of Tillerson’s appointment as America’s top diplomat, hailing the news as an indication that Trump would fulfill his campaign promises to improve U.S.-Russia relations. “The choice of Tillerson is a sensation,” Alexei Pushkov, a pro-Kremlin Russian lawmaker, said last December. “Judging by the appointments to the key posts in the administration, Trump wants to see a decisive and strong America, but does not see reasons for conflicts with Russia.”

But since Trump’s inauguration and Tillerson’s Senate confirmation, the relationship between the U.S. and Russia has frayed. After Congress forced the president’s hand in leveling a fresh round of sanctions against Moscow in response to Russian election interference, the two countries have engaged in a bout of retaliatory measures. In July, Putin ordered the U.S. to cut its diplomatic staff in Russia by 755. Weeks later, the State Department directed Russia to shutter three diplomatic sites in Washington, D.C., San Francisco, and New York City. The tit-for-tat diplomacy comes amid heightened tensions as a series of escalating conflicts play out on the world stage, pitting U.S. and Russian interests against each other in North Korea, Ukraine, Iran, and Syria.